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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21BrN2O3S
Molecular Weight 437.351
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AK-7

SMILES

BrC1=CC(NC(=O)C2=CC=CC(=C2)S(=O)(=O)N3CCCCCC3)=CC=C1

InChI

InChIKey=IYAYHZZWYNXHEQ-UHFFFAOYSA-N
InChI=1S/C19H21BrN2O3S/c20-16-8-6-9-17(14-16)21-19(23)15-7-5-10-18(13-15)26(24,25)22-11-3-1-2-4-12-22/h5-10,13-14H,1-4,11-12H2,(H,21,23)

HIDE SMILES / InChI

Molecular Formula C19H21BrN2O3S
Molecular Weight 437.351
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23200855 | https://www.ncbi.nlm.nih.gov/pubmed/27372638 | https://www.ncbi.nlm.nih.gov/pubmed/26089639

AK-7 is a brain penetrant selective SIRT2 inhibitor. AK-7 exerts neuroprotective properties in vitro and in vivo models of neurodegenerative diseases (Huntington’s, Parkinson’s and Alzheimer’s disease).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
15.5 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
A brain-permeable small molecule reduces neuronal cholesterol by inhibiting activity of sirtuin 2 deacetylase.
2011 Jun 17
The sirtuin 2 inhibitor AK-7 is neuroprotective in Huntington's disease mouse models.
2012 Dec 27
The sirtuin inhibitor cambinol impairs MAPK signaling, inhibits inflammatory and innate immune responses and protects from septic shock.
2013 Jun
Inhibition of Sirtuin 2 exerts neuroprotection in aging rats with increased neonatal iron intake.
2014 Nov 1
Aging-related rotenone-induced neurochemical and behavioral deficits: role of SIRT2 and redox imbalance, and neuroprotection by AK-7.
2015
Sirtuin-2 inhibition affects hippocampal functions and sodium butyrate ameliorates the reduction in novel object memory, cell proliferation, and neuroblast differentiation.
2016 Dec
SIRT2 inhibition exacerbates neuroinflammation and blood-brain barrier disruption in experimental traumatic brain injury by enhancing NF-κB p65 acetylation and activation.
2016 Feb
Sirtuin 2 Inhibition Improves Cognitive Performance and Acts on Amyloid-β Protein Precursor Processing in Two Alzheimer's Disease Mouse Models.
2016 Jun 30
Aging-related 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurochemial and behavioral deficits and redox dysfunction: improvement by AK-7.
2016 Sep
Patents

Patents

Sample Use Guides

mice: i.p. 20 mg/kg twice daily. rats: intracerebral injections into the substantia nigra 5 μg/side per day.
Route of Administration: Other
Treatment with 1-10 uM AK-7 resulted in protection of neurons in an in vitro model of Huntington's disease
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:34:32 GMT 2023
Edited
by admin
on Sat Dec 16 09:34:32 GMT 2023
Record UNII
308B6B695N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AK-7
Common Name English
BENZAMIDE, N-(3-BROMOPHENYL)-3-((HEXAHYDRO-1H-AZEPIN-1-YL)SULFONYL)-
Systematic Name English
Code System Code Type Description
CAS
420831-40-9
Created by admin on Sat Dec 16 09:34:33 GMT 2023 , Edited by admin on Sat Dec 16 09:34:33 GMT 2023
PRIMARY
PUBCHEM
1328033
Created by admin on Sat Dec 16 09:34:33 GMT 2023 , Edited by admin on Sat Dec 16 09:34:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID30194926
Created by admin on Sat Dec 16 09:34:33 GMT 2023 , Edited by admin on Sat Dec 16 09:34:33 GMT 2023
PRIMARY
FDA UNII
308B6B695N
Created by admin on Sat Dec 16 09:34:33 GMT 2023 , Edited by admin on Sat Dec 16 09:34:33 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY